Intermolecular and Intramolecular Ketone–Nitrile Reductive Coupling Reactions Promoted by TiCl4–Sm System

The intermolecular and intramolecular reductive coupling reactions of ketones with nitriles have been successfully promoted by low-valent titanium prepared by the TiCl4–Sm system. Substituted ketones, monocyclic α-amino alcohols and monocyclic amines composed of a number of substitution patterns have been prepared in good yields at room or THF reflux temperature under neutral conditions. The procedure can avoid over reduction of the resulting of ketones, α-amino alcohols or amines. The crystal structures of two monocyclic α-amino alcohols are reported.